Waterfront vacation rentals in Summerland Key
Find and book unique waterfront rentals on Airbnb
Top-rated waterfront rentals in Summerland Key
Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Summerland Key waterfront rentals
Waterfront apartment rentals
Apartment in Key West
4.92 out of 5 average rating, 175 reviewsKW Luxury 2/2 Beachfront resort Tropical Oasis
Apartment in Key West
4.89 out of 5 average rating, 136 reviewsKey West Beachside 1400sf, 2 Bedroom Condo
Apartment in Marathon
5.0 out of 5 average rating, 8 reviewsGated Oceanfront Heated Pool
Apartment in Key West
4.94 out of 5 average rating, 16 reviewsOceanfront Condo in Key West
Apartment in Key Colony Beach
4.81 out of 5 average rating, 80 reviewsBeachside Unit 22 - Private Beach on Atlantic
Apartment in Key West
4.89 out of 5 average rating, 46 reviewsPenthouse in Paradise
Apartment in Marathon
4.95 out of 5 average rating, 38 reviewsDock POOL Kayaks Bikes Beach2mi WalkToStores
Apartment in Marathon
5.0 out of 5 average rating, 5 reviewsMarathon Studio on Lovely Resort
Waterfront house rentals
Home in Key Colony Beach
4.96 out of 5 average rating, 136 reviewsBeautiful open plan remodeled home in Key Colony
Home in Cudjoe Key
4.87 out of 5 average rating, 46 reviews*Emerald Seas*-Florida Keys Ocean Front Paradise!
Home in Cudjoe Key
5.0 out of 5 average rating, 24 reviewsParadise in Cudjoe! Perfect Family Home!
Home in Cudjoe Key
4.82 out of 5 average rating, 49 reviewsSpanish Queen @Venture Out
Home in Cudjoe Key
4.95 out of 5 average rating, 19 reviewsConch Cabana in Paradise 23 miles outside Key West
Home in Cudjoe Key
4.85 out of 5 average rating, 13 reviewsRise-N-Shine
Home in Cudjoe Key
4.86 out of 5 average rating, 28 reviewsKeys Island Villa - Venture Out Home 354
Home in Big Pine Key
4.89 out of 5 average rating, 64 reviewsFishermen`s Paradise
Waterfront condo rentals
Condo in Key West
4.89 out of 5 average rating, 149 reviewsLarge waterfront 2/2 end unit with boat slip
Condo in Key West
4.85 out of 5 average rating, 143 reviewsAnchor Drop modern elegance upgrades throughout vi
Condo in Key West
4.83 out of 5 average rating, 243 reviewsLa Dolce Vita, Old Town Steps to Duval! 3 blks bch
Condo in Key West
4.96 out of 5 average rating, 76 reviewsHidden Beach unit 1 The Perfect Place to stay
Condo in Key Colony Beach
5.0 out of 5 average rating, 27 reviewsSea-Esta Condo beach and pool
Condo in Marathon
5.0 out of 5 average rating, 7 reviewsOcean Potion NEW 1B/2B 3Balconies Ocean View
Condo in Key West
5.0 out of 5 average rating, 31 reviewsGorgeous Ocean View in Paradise
Condo in Key West
5.0 out of 5 average rating, 8 reviewsPremium Ocean View Residence
Quick stats about waterfront rentals in Summerland Key
Total rentals
120 properties
Rentals with a pool
80 properties have a pool
Pet-friendly rentals
50 properties allow pets
Family-friendly rentals
100 properties are a good fit for families
Total number of reviews
2.2K reviews
Nightly prices starting at
$110 before taxes and fees
Destinations to explore
- Key West Vacation rentals
- Varadero Vacation rentals
- Naples Vacation rentals
- Miami Vacation rentals
- Miami Beach Vacation rentals
- Havana Vacation rentals
- Fort Lauderdale Vacation rentals
- Boca Raton Vacation rentals
- West Palm Beach Vacation rentals
- Sarasota Vacation rentals
- Anna Maria Island Vacation rentals
- Tampa Vacation rentals
- Waterfront rentals United States
- Waterfront rentals Florida
- Waterfront rentals Key West
- Waterfront rentals Florida Keys
- Waterfront rentals Marco Island
- Rentals with beach access Summerland Key
- Rentals with a patio Summerland Key
- Pet-friendly rentals Summerland Key
- Rentals with a washer and dryer Summerland Key
- Rentals with pools Summerland Key
- Monthly Rentals Summerland Key
- Rentals with outdoor seating Summerland Key
- Family-friendly rentals Summerland Key
- Rentals with a hot tub Summerland Key
- House rentals Summerland Key
- Rentals with a kayak Summerland Key
- Kid-friendly rentals Summerland Key
- Waterfront rentals Monroe County
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes